A method for generating content links between a first digital file and a second digital file by detecting a content feature of a first digital file segment of the first digital file during playback of the first digital file segment of the first digital file, searching an index of a plurality of content features for a plurality of segments including a second digital file segment of the second digital file, and dynamically generating a link between the first digital file one segment of the first digital file and the second digital file segment of the second digital file when a content feature of the first digital file segment of the first digital file is related to the content feature of the at least one segment of the second digital file.